Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Vanessa Barcus

I originally went to college for Economics, and later business school, thinking that I’d go into finance. I look back and laugh at how I didn’t know myself as well back then. I think I was trying to appease my father. Luckily I had a school administrator who recognized the creative in me, and encouraged me to take an internship in the fashion industry. I was hooked. I suppose I can’t say I wish I had started sooner, because in reality my entire career was in creative fields from that point on, from fashion to advertising to retail and jewelry design. Read more>>

Dr. Sarah Zaldivar.

If I could go back in time, I definitely wish I would have started a business sooner rather than later. I didn’t realize it at the time, but I am built for entrepreneurship. I just used to think that entrepreneurs were intimidating mean bosses, and I never imagined that I could be that person. I suffered greatly with anxiety, self-confidence, and low esteem, and I hated confrontations (I still do by the way), and for those reasons I thought I could never be in a leadership position. Little did I know that true leaders had none of the traits I ascribed to them in my mind. Read more>>

Keith Trost

I would admit I wish I had started my business sooner versus later. I was in several companies with a brother-in-law, we were not on the same page, and I was unhappy most days, yet I wouldn’t take the leap to start my coaching business. Then, in late 2016, the brother-in-law did a hostile takeover, and I was out. My future had become accessible, and in 2017, I flew to Detroit to join a group of entrepreneurs who facilitated the implementation of EOS® (Entrepreneurial Operating System), and I became a Professional EOS® Implementer. Read more>>

Mardia Brown

Honestly, I wish I had the guts to start my skin care brand much younger, I think I would be further along by now if I did. However, over the years I have learned a lot more about the ins and outs of business I didn’t know years ago. So starting it later that what I should’ve might have been a good thing. Read more>>

Brigitte Schambon-Kiser Schambon-Kiser

Yes, I wish I would’ve started my own business earlier in life. I also wish I would’ve continued shooting and diving into the field at full force from an early age. But If only I could turn back time, I would’ve done things differently. In my 20’s, I was working a 9-5 job just to pay the bills. I had gone to school for an Interior Design degree, but never pursued it as a career because i wasn’t passionate about the profession. I just really had aspirations of becoming a professional photographer one day because I had an intense interest and a deep connection to the art… Read more>>

Stephani Shaner

Oh, absolutely! I would have started my business many years ago! I think people fear starting a business because there is a certain amount of risk involved. I have no regrets with the business I started because it has brought amazing things to my life, so I wouldn’t view it as a regret that I started later than I could have. I appreciate my timeline in this industry because it’s mine and everything happens for a reason. However, knowing what I know now, to go back in time would mean an easy decision to start sooner and let it change my life in all the positive ways it has. Read more>>

Jen McDonald

I am very lucky to be heading into my 14th year of business. Looking back at my success, I feel my progress has been a wonderful slow burn. In 2008 I retired from my career as an educator to be a full-time mom. As wonderful of a decision as that was, my need to express my creativity fueled my mission to create something of my own – that’s how my business began! In the beginning I focused on my first passion, photography, but slowly began to work more and more on graphic design. Read more>>

Tamara Tribble M.Ed.

I wish I had started my business earlier because I learned that we will not get rich punching the clock. Real wealth is tied to entrepreneurship! This is especially true for minorities in America. Read more>>

Bailie Kate

I would have definitely started my business even sooner. I think like most people, I was ok with being “comfortable” for the longest time. I was afraid to take that leap of faith and face the possibility of failing or not achieving the level of success I was hoping for. I think like a lot of people, during the pandemic I was able to re evaluate what is important to me and prioritizing my well being over what I had previously perceived as success. I had been at a very popular salon for 5 years, which was great at first, and I was incredibly busy. So what did I have to complain about, right? Read more>>

Bobby DeLancellotti

Our nonprofit, the Estero Bay Kindness Coalition was only 2 years old when the pandemic hit. Prior to the pandemic we were implementing 1 food program, Got Your Back, in several elementary schools in the San Luis Obispo Unified School District. Got Your Back provides meals on the weekends for food insecure kids who rely on “reduced/hot lunch” at school to eat during the week, ensuring they don’t go hungry on Saturdays and Sundays. Read more>>

Jasmine Armenta

Looking back, I’m happy that I trusted myself and waited until I felt ready or I don’t know that I would’ve been as successful. However, I do wish that I had started this journey sooner because although it’s been tough, it’s been one of the best decisions that I have ever made! I had been working for European Wax Center in Pacific Beach for 5 years up until the Pandemic happened and everything shut down. I was comfortable and happy there. I liked showing up to do what I loved and then being able to leave and forget about work. I was told by so many people that I needed to open up my own business for years but I didn’t feel ready. Read more>>

Amanda Sullivan

Yes, If I could go back in time I would have started my business sooner because I would be a popular MUA and have my name all over social media platforms. Looking back as a little girl I did see my mom do makeup, she was so dedicated that I thought she would do it full time even though she worked at the Fashion Fair counter inside of Macy’s. Seeing my mom as a MUA I wanted the experience to make any woman feel beautiful on any special day or occasion. Read more>>

Dawn Rice

Although we officially opened the Write On! storefront in March of 2020, Write On! originated in my home in 2013. I offered summer camps and weekly workshops for elementary, middle, and high school writers. The timing was just not right then to open a storefront, despite the challenges of having a home business. There have been times that I wished we would have taken the leap then, who knows where we’d be now. Equally, had we waited just a few more months longer to open, well, I am pretty sure Covid would have stopped us from opening for some time. Read more>>

Willie Johnson

In many ways, I regret that I did not begin pursuing an art career a lot sooner. I’ve wanted to be a digital artist since my early teens. I enjoyed the freedom and felt kind of like I lived in a dream. There was so much inspiration in all forms of media and entertainment that it seemed to just be non-stop. Somehow it felt like the right moment for me to grow into a young adult and witness the brilliance. Read more>>

Sleepless The Poet

Definitely sooner. I’m thirty-one and I’ve been writing my whole life, but admittedly did not fully grasp or have the foresight of how powerful social media was going to be. I was posting on Instagram in 2011. Just posting pictures I had taken that I thought were good; not even writing poems to them yet. Had I known what Instagram was going to turn into and that entire careers would be made from it, I would’ve started pairing the poems a lot sooner. Read more>>

Brandi Moss

Well I started creating as a teenager, I didn’t really hone in on my creativity. It was always more of a hobby for me and I am 100% self taught. I wish I had taken time when I was younger and explore classes to learn various techniques. I think if I had spent more time and effort learning other skills when I was younger I would be in a different place than I am today. Not that it’s a bad thing being where I’m at in this point of my life,but I think I might be further along in my career had I done things a little bit differently. Social media didn’t exist 30 years ago when I was starting out and that has made a huge impact in the way small businesses operate in todays world. Read more>>

The Bella Locas

All of us started singing and performing at a young age, separately of course, so finding each other kind of felt like a perfect match. We all share a love for performing and at first we wanted to form a band as a joke, but it quickly became real as we take our creative and artistic endeavors really seriously. It’s overwhelming how much support we’ve received from the local community and our friends, abundance mindset am I right? Read more>>

Maggie Lee

No l don’t actually, I strongly believe that you can start whatever you want to do at any point in your life. Sure, it could be nice to start things but we have so much time, truly. And I’m going to enjoy that time and be grateful I’m doing it now, instead of wishing I did it sooner. I love what I do, and the experiences I have made (good and bad) cement just how much I enjoy art, the pop ups and being involved and around other creatives! Read more>>

Lucy Sando

God’s timing is the best timing. I believe if I were meant to start sooner I would have. The time I began creating my own music was when I was fresh out of high school as a freshman in college. Since then I have undergone multiple life experiences that I don’t believe I was prepared for mentally at the time of the occurrences . Now as I enter my prime I am mentally mature and able to undergo what comes with the entertainment industry. If I could change anything about my experience I would emerge myself 100% with no distractions. Read more>>

Rashad Groce

I would start exactly where and how I did. I began my journey as a musician in college. The one thing that I would change is my mindset of understanding that even being a musical artist that it is still a business. All I care about was making the music and not really promoting it or having a hand in controlling my own destiny. I was with a label and they did promote me but I was an artist amongst other artist on the label. Had I known then what I know now, I would have utilized the machine of the label more to my advantage and been alot more involved in my own narative for the future. Read more>>

Debra Gibson-Welch

I wish I started my business sooner because it takes years to build a reputation and scale as a business. It depends on the type of business, and how you started and scaled. It takes years to establish a credible reputation, and build a strong customer base that will stay and grow with you. Read more>>